Here are the last two smarmy-guy-with-hat Willys ads I found.

"RamblinRover Luxury-Yacht" (ramblininexile) 11/04/2014 at 15:54 • Filed to: None

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I'm sorry I couldn't find a copy of the second one big enough to read, because while the first one is funny ("to men of experience", "the Beautiful Sister of the Famous Jeep"), I think the second has got to be a gold mine. "This my wife would never understand"? Oy.

Arch Duke Maxyenko, Shit Talk Extraordinaire > RamblinRover Luxury-Yacht 11/04/2014 at 15:57

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That dude is the smarmiest

RamblinRover Luxury-Yacht > Arch Duke Maxyenko, Shit Talk Extraordinaire 11/04/2014 at 16:01

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But there's like... different faces on these ads. Either Smarmy Hat Dude is the Grand Master of Disguise, or there's a secret Fedora Cabal that was backing Willys the whole time.

Arch Duke Maxyenko, Shit Talk Extraordinaire > RamblinRover Luxury-Yacht 11/04/2014 at 16:06

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You've stumbled onto something that must be exposed to the world!

StoneCold > RamblinRover Luxury-Yacht 11/04/2014 at 16:08

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I have greatly enjoyed the terribleness of these. It seems that all of these ads just scream "ONLY PUSSIES DRIVE CRESTLINERS, THIS IS A JEEP MAN'S CAR", as much as a Fifties ad can scream.

RamblinRover Luxury-Yacht > StoneCold 11/04/2014 at 16:12

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They have a bunch more of another funny sort which are ridiculous in the same vein as the Grenada vs. Mercedes ads - hits at Cadillac for including features that a Willys has, etc.

StoneCold > StoneCold 11/04/2014 at 16:14

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Also, "To Men Of Experience"

Translated: GET YOUR ASS OUT OF THAT MODEL T AND INTO AN AERO, YOU VIRGIN!

ranwhenparked > StoneCold 11/04/2014 at 18:11

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And later, Chrysler would try something somewhat similar with Eagle, to similar results.